Sightseeing
From quirky tours to can’t-miss landmarks, sightseeing in The Florida Keys is anything but ordinary - on island or at sea. Hop on a trolley or the iconic Conch Train, set sail on a charter, or wander museums filled with history, art, and stories you couldn’t make up if you tried. Key West’s haunted tours add a spooky thrill, while scenic drives and hidden stops up and down the island chain reveal the Keys’ offbeat charm. These listings connect you with the guides, tours, and attractions that turn “just looking around” into a true island adventure.
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Islamorada
Easy Livin' Charter Boat
Custom boat tours and fishing adventures with local legend Captain Augie in Islamorada.
Islamorada
Anchors Away Boat Rentals and Tours
Anchors Away Boat Rentals & Tours offers a diverse fleet of over 30 boats, including center consoles, deck boats, and pontoons, available for flexible rentals ranging from 2-hour to monthly durations, with GPS-equipped vessels and optional add-ons like snorkeling gear and GoPro cameras.
Key West
Key West Sandbar Tours
Escape to hidden sandbars with Key West Sandbar Charters — private boat tours (small or large groups), crystal waters, sun, fun & photo-perfect views.
Marathon
Fishing Kings
Marathon Fishing Kings — private reef, wreck & offshore fishing charters in Marathon, where expert guidance meets trophy-fish potential.
Key West
Reel Paradise Charters
Experience unforgettable days on the water in the Florida Keys with private and shared charters from Key West.
Key West
FishMonster & IslandJane Charters
Key West’s premier fishing and adventure charters, offering everything from party boat fishing to private eco-tours and sunset sails.
Key West
Fly-Key West Helicopter Tours
Soar above Key West in a helicopter tour — scenic, adventurous, unforgettable.
Islamorada
AquaBlue Adventures Sandbar Charter & Boat Tours
AquaBlue Adventures: Your go-to for expert-guided snorkeling, paddleboarding, and private eco-charters in the Florida Keys.
The Lower Keys
Sandbar Somewhere Charter
Sandbar Somewhere Charter, led by Captain Hoyt Watkins, offers relaxed inshore and backcountry fishing trips around Summerland Key and Big Pine Key.
Key West
Key West Ghost Tours: Southernmost Shadows and Ghosts
Discover Key West’s haunted history with a chilling walking ghost tour through cursed graveyards, eerie historic sites, and stories of restless spirits in the heart of Old Town.
Key West
Dauntless Excursions
Dauntless Excursions offers private, customizable charters from Key West, featuring activities like lobstering, snorkeling, reef fishing, and sandbar hopping aboard the 32-foot Dauntless vessel.
Islamorada
Bamboo Charters
Bamboo Charters, led by Captain Matt Bellinger, offers personalized fishing, snorkeling, sandbar, and sunset excursions aboard the "Chubby Mermaid," providing unforgettable experiences in the Florida Keys.
Key West
Salty Bottom Boats
Salty Bottom Boat — private custom charters in Key West for sandbar parties, sunset cruises & island adventures.
Marathon
Duck Key Watersports
Duck Key Watersports offers unforgettable on-the-water adventures in the Florida Keys, from jet skis and paddleboards to kayaking and snorkeling.
